Preparation of nucleoside phosphoramidite intermediates

Details Preparation of nucleoside phosphoramidite intermediates Preparation of nucleoside phosphoramidite intermediates

C - Chemistry, Metallurgy

07

H

260/229.1, 260/3

C07H 19/04 (2006.01) C07F 9/65 (1985.01)

Patent

CA 1268173

NOVEL PREPARATION OF NUCLEOSIDE PHOSPHORAMIDITE INTERMEDIATES Abstract Nucleoside phosphoramidite intermediates are prepared by a chemical reaction represented by a formula: X-O-?-Y + weak acid + (I) (II) Image (III) Image (IV) In addition, nucleoside phosphoramidite inter- mediates are prepared by a chemical reaction represented by the following formula: X-O-?-Y + weak acid solvent , intermediate (I) (II) intermediate + Image (III) Image (IV) In both of the above chemical reaction formulas, X is a phosphate protecting group; each Y is a secondary amino group; ; Z is a hydroxy protecting group; the weak acid is capable of selectively protonating only one amine of the secondary amino groups; each A is selected from a group consisting of -H, -OH, and -OZ; B is selected from a group consisting of natural and unnatural purine and pyrimidine bases: G is a heterocyclic base protecting group; each D is selected from a group consisting of -H and -OZ; E is selected from a group consisting of -OR and -OZ, provided that (a) when both As are the same and are -H or -OZ, then E is -OH and (b) both As and E cannot all simultaneously be equal; n is a number from 0-2; r, s, and t are each 0 or 1, provided that r + s + t = 2; the solvent is capable of (a) solubilizing I, II, and III and (b) allowing the reaction to proceed; and III is present in a molar concentration at least equal to the molar concentration of reactable I. The present invention provides a simplified methodology which is readily accessible to automation and, if a manual solid-phase deoxynucleotide (DNA) and/or ribonucleotide (RNA) synthesis is preferred, to use by a non-chemist. More particularly, the present invention encompasses a convenient method for preparing deoxy- nucleoside and ribonucleoside phosphoramidite inter- mediates in situ from corresponding natural and unnatural nucleosides.

473048

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